Mastermind
by jheaton
Summary: Dean Pelton needs Jeff Winger to feel better about being at Greendale, and he needs Annie Edison to make it happen.
1. Chapter 1

Craig Pelton was an unusually passionate man, not to mention a man of unusual passions, and the thing he was most passionate about (and, some would say, his most unusual passion) was Greendale Community College. Greendale had changed his life; he had arrived there immediately after high school as an aimless, mostly friendless nerd, and had left two years later energized with purpose. He would become a community college educator. He would follow in the footsteps of Will Anderson, Greendale's dean, who had become his mentor and friend, who had guided and encouraged him, and taught him to believe in himself.

Two years later he was back at Greendale with a degree in English and Education and a job in the school's writing center. By day, he tutored students in the finer points of grammar and compositional skills, and learned all he could about community college administration from Dean Anderson. In his spare time, he worked toward a Student Affairs in Higher Education Master of Science degree from Colorado State. It had taken four years of hard work and a lot of trips between Greendale and Fort Collins, but he'd graduated with honors, and when Dean Anderson retired two years later, Pelton's years of preparation and his obvious (and obsessive, some said) love for the institution made him the logical choice to be the next Dean.

The new dean was firmly convinced that Greendale Community College could be a first-rate institution of higher learning, but was all too aware that most people didn't see it that way. But he was sure that with enough effort on his part, people would eventually come around to his point of view. And so, as he liked to say, he beat on, a boat against the current, but one who refused to be borne back into the night, at least not ceaselessly. (He had written his senior thesis on Fitzgerald.)

At the beginning of each school year, the dean would make two lists, one that ranked the incoming students in order of physical attractiveness, and another ordered by how helpful they might be in improving Greendale's reputation. He had found a few gems among this year's crop, many of whom, oddly enough, had ended up in a Spanish study group together: Troy Barnes, a former high school football star who was just what the struggling Greendale football program needed; Annie Edison, a real go-getter who could always be counted on to volunteer for pretty much anything; Pierce Hawthorne, the fifth richest man in the state and thus a lucrative source for future donations to the school.

And then there was Jeff Winger, who was near the top of both lists. Jeff was a very attractive man, and one who positively oozed charisma. He had founded and seemed to be the leader of the Spanish study group Barnes, Edison, and Hawthorne were part of. And what a speaker! Winger had a way with words that could convince a legless man to get up and walk. The dean had never expected to find himself nodding in agreement as he listened to someone compare his beloved school to an insane asylum, but that's how good Winger was. Unfortunately, that comparison was one of the nicer things the dean had heard him say about Greendale; Winger's attitude toward the college ranged from grudging tolerance to seething hatred, and with that kind of attitude, Jeff was unlikely to be of much use to the school. Still, Pelton had to try. He had, quite to his own surprise, successfully blackmailed Jeff into convincing Troy to join the football team, but that wasn't a trick he'd likely be able to repeat. So he took to observing Jeff more closely, now looking not just at his body but also for a way to break his resistance to supporting his school.

It was about a week later when he spotted what could possibly be a chink in Winger's armor. He had seen Annie Edison confront Jeff in the hall and demand that he attend a Mexican Halloween celebration she was throwing in the library. Winger had refused at first-which was a little surprising, as Annie was a very attractive young lady (albeit in a buttoned-down way sort of way) and Jeff struck him as the kind of person who would really enjoy a Mexican Halloween-but to the dean's astonishment, Jeff relented almost immediately as Annie burst in tears in front of him. And hadn't he just seen the pair together outside the pep rally a few days earlier, Jeff's arm slung around Annie's shoulders?

He thought maybe he'd misread the situation when, a few weeks later, Annie was unable get Jeff to join her on the Greendale debate team. A bribe had ultimately done the trick, but getting him on the team turned out to be only half the battle. The dean had watched with disappointment as Winger put forth next to no effort in the debate against City College despite Edison's obvious disapproval. Afterward, though, he happened upon City College's star debater, Jeremy Simmons, taunting Jeff and Annie in the hallway outside the gymnasium. His attacks on Jeff had no effect, but as Simmons turned his acid tongue on Annie, Jeff's entire demeanor changed. With a single glance at Annie's crestfallen face, Winger let loose on Simmons and led Annie away to prepare for the conclusion of the debate. Interesting.

And then, the kiss. Oh God, the kiss. The dean had rarely seen anyone as gobsmacked as Jeff after Annie kissed him to win the debate. But it wasn't that deer-in-the-headlights look that excited him so much, it was the look that followed. It was a look that mingled embarrassment and fear, that communicated quite clearly that Jeff had never considered that there might be someone with such power over him, and that he had no idea as to how he might be able to keep it from happening again.

That settled it. If Jeff Winger was a man who could get anyone to do anything he wanted, then Annie Edison was Jeff Winger's Jeff Winger. His weakness in the face of her distress and his obvious attraction to her meant she, and perhaps she alone, could convince Jeff to use his talent and his influence for the greater good of Greendale. As the weeks passed, though, it became evident that there were limits to Annie's influence. Jeff had displayed no interest at all in the STD Fair despite Annie's obvious enthusiasm for it. It seemed that unless she was visibly upset, or was kissing him, Annie was no more able to get Jeff to do something than the dean was. The former was not of much use; Jeff knew better by now than to antagonize her himself, and jackasses like Jeremy Simmons were in short supply.

As for the latter, it seemed as though Jeff was going to pains to avoid acting on his obvious attraction to her. In fact, Pelton had watched Jeff flirt with his assistant Sabrina right in front of Annie. (Of course, even if he had tried anything with Annie, she might well have died of embarrassment, if her reaction to the anatomically correct penis model was any indication.) Their time together in Group Study Room F notwithstanding, Jeff was spending time with everyone _but_ Annie, even Ben Chang, of all people. Which was a problem. If they were never together there wouldn't be any kissing, and he _needed_ them to be kissing. He was going to have to take matters into his own hands.


	2. Chapter 2

The best plans, Dean Pelton reasoned, were the simplest ones. The last time Jeff and Annie had kissed, they were both on the debate team, so the dean figured that if he got them working together on some other activity, kissing would inevitably follow. Annie was already involved in more organizations than anyone else on campus, so it was really just a matter of finding one that he could convince Jeff to join. But which one? The Greendale Astronomical Society? Chess and Games Club? Hillel?

The _Greendale Gazette Journal Mirror_. It was perfect. The paper needed an editor-in-chief, which would appeal to Jeff's vanity; it came with a private office with a sofa and a desk, which would appeal to his materialism and his desire to get as far away from the rest of the student body as possible; and it carried an English credit, which would appeal to his laziness. And as a former lawyer, he probably wrote well enough to make him a credible choice for the job. He added the newspaper offices to the list of places around campus he planned to install surveillance cameras.

The dean was proud of that part of the plan. He needed to continue observing Jeff and Annie, so he could track the progress of the plan and make any small adjustments that might be necessary to keep it on track. The cameras were the perfect way to do that, and since he had already arranged for cameras to be installed in the women's bathrooms to cut down on the toilet seat theft problem-never let it be said he didn't respond to the concerns of the student body!-it would be easy enough to get the techs to install them in other places around the campus as well. Cameras would be placed in the Spanish classroom, the cafeteria, various hallways and common areas Jeff and Annie were known to frequent, the parking lots, and of course Group Study Room F. The study room would be wired for sound as well; he had wanted microphones installed alongside all the interior cameras, but the budget just wouldn't support the expense. The camera in the Spanish classroom would at the insistence of the union be turned off while class was in session; they also had refused to let him to place cameras in staff offices. But he could live with that. How likely was it that anything would happen in a professor's private office that would have an impact on the plan?

* * *

Three weeks! Slater must have made her move the same day he'd offered Jeff the editorship. The dean was more than a little surprised; relationships between students and professors were rare at Greendale, and Slater in particular had, to his knowledge, had never been known to dilly-dally with the student body, even students with bodies as nicely developed and irresistibly touchable as Jeff's. On the other hand, maybe she was just really good as keeping her dalliances under wraps.

The relationship was dangerous. Not because he expected it to last; on the contrary, he expected it to end quickly and brutally. Slater was a whiz with numbers, but normal human emotions seemed beyond her. He fully expected her to dump Jeff sooner or later, and probably in the most callous and dismissive way possible. Therein lay the problem. Once dumped, Jeff might turn to Annie for comfort, but that would make Annie Jeff's rebound, and you can't really count on rebound relationships to last. In order for the plan to work, Jeff would have to break up with Slater, not vice versa. And he knew just how to make it happen. All he had to do was engineer a relationship between Annie and some other student. Jeff would of course be consumed with jealousy, and would be driven to steal Annie away from the other guy.

The other guy in the scenario, the dean decided, would be Vaughn Miller. To someone as straight-laced as Annie, Vaughn would seem edgy and slightly dangerous rather than pot-addled and harmless. She would find his ridiculous songs sweet. And it didn't hurt that he had a nice body. Really nice. Best of all, it was well known on campus that Jeff loathed Vaughn, so seeing Annie with him would be particularly infuriating.

The dean stopped to talk to Vaughn in the cafeteria a few days later, ostensibly to compliment him on his impressive hacky sack skills but really to casually draw his attention to Annie when she walked past on the way to her regular table. He seemed interested, and sure enough, the next day the dean saw Vaughn serenading Annie on the quad, Annie reveling in the attention, and Jeff looking on with distaste. And a day or two after that, he caught Jeff lurking behind a bush watching in disgust as Vaughn taught Annie to ride a skateboard. Success!

Except when all was said and done, Annie and Vaughn were still an item. The dean had been right that Jeff would want to break up the new couple, but Jeff tried to set her up with Troy Barnes instead of himself, and the whole thing had blown up in his face. The dean had underestimated Jeff's commitment to his relationship with Slater. And, apparently, Annie's and Vaughn's commitment to one another. That made things a lot trickier.

It was now clear to the dean that both Jeff and Annie would need to be single before they could get together. In Jeff's case, that would be no problem; the dean expected Slater to dump Jeff any day now, so he would just sit back and wait for the inevitable while concentrating on the Annie side of the equation. It was evident that neither she nor Vaughn could at this point be manipulated into breaking up, and frankly he was a little scared to try after seeing her reaction to Jeff's meddling. It was possible that at some point Annie would tire of Vaughn's lack of structure, or that he would rebel against her love of the same, but he didn't want to bet the farm on it. What he needed was something that he could introduce from behind the scenes that would radically change the dynamic of the relationship for the worse. But what?

The answer came in the form of an article in _Community College Week_ about the explosive growth of intercollegiate footbag at the community college level, in which the Caesar Rodney Campus of Delaware Technical & Community College was named as one of the best teams in the country. Dean Pelton happened to know the dean of the Rodney Campus; they had been classmates at Colorado State. He was sure his fellow dean would be very interested to hear about a talented hacky-sacker languishing at a school whose budget was too tight to fund a new athletic team. He was equally sure that Vaughn would jump at the chance to be on the number one community college hacky sack team in the country, even if he had to move 1,700 miles away to do so. Sure, he and Annie might try a long-distance relationship, but the dean had been a community college educator his entire adult life and had lost count of how many relationships he seen crumble after one person transferred and the other stayed behind. And someone like Annie would never move across the country just to attend a different community college.

While he waited for Rodney Campus to take the bait, the dean continued to observe Jeff and Annie, more out of habit than for any particular reason. As expected, Slater had dumped Jeff; tellingly, Jeff was now not dating anyone. Annie, meanwhile, was still dating Vaughn. The good news on that front was that the dean had seen her taking a long and appreciative look at Jeff's naked backside during his pool game with Coach Bogner, giving him some hope that she might be coming to see Jeff as someone who could be more than just a good friend. On the other hand, he also had seen her repeatedly slapping Jeff on the arm and slamming his head into the study room table, so he wasn't quite sure what to think.

Toward the end of April, the dean arranged for Vaughn and his friends to stage a hacky sack demonstration during the school's annual Arbor Day Festival, and suggested to his former classmate that he come to Greendale to see Vaughn in action. He did, bringing with him the athletic director and the captain of the Rodney Campus footbag team. All were suitably impressed, and the athletic director told the dean that he was going to fight hard to get Vaughn an invitation to join his team. Dean Pelton could not have been more excited. Greendale's Golden Age was right around the corner!

* * *

Dean Pelton collapsed into his chair at the end of the worst day of the worst month of his ten years as an educator. The entire month of May had been one disaster after another. Cleaning up after the paintball debacle had blown a huge hole in his budget. The revelation that Ben Chang was a fraud had made the dean look like a fool, since it was he who had hired Chang in the first place. And worst of all, his plan to get Jeff and Annie together was in shambles. First, Jeff had slept with his study group friend Britta Perry during the paintball war. They had given no signs since that the sex meant anything to either of them, but in the surveillance video they both seemed to be enjoying it, and his fear that perhaps it _had_ meant something to them increased each time he watched it.

Then, in the last week of the semester, Jeff and Annie had had a huge fight. Annie had told the dean that Chang was a fraud, and when Jeff found out, he had blown up and forced her out of the study group. By the next day, things had improved somewhat, and in fact Jeff had gone so far as to kick in the door to Chang's office when he thought Chang was threatening her. The dean didn't know exactly what had happened in Chang's office-damn that union!-nor what Jeff and Annie had said to each other in the hallway afterward, but there definitely appeared to be a certain awkwardness between them.

Nevertheless, there had been reason to be optimistic on the last day of classes. Jeff had seemed to be genuinely happy to be on campus for a change, and it had taken no effort at all to convince him to attend the Tranny Dance being held the following evening. Around noon, Vaughn had come by his office to inform him of his invitation to join the Rodney Campus footbag team and his intent to transfer there. It was everything he had imagined. The following evening, Jeff and a newly single Annie would find themselves together at a romantic formal dance. Kissing would, he was sure, soon follow.

The next day was when it all went to hell. Annie had come into his office and informed him that she was going to follow Vaughn to Delaware. The dean had tried his best to talk her out of it, pointing out that it was a lateral move at best, that admission officers would wonder why she had made the change, but she was firm. Something about "living in the moment." He had watched from the dance floor later that night as she said goodbye to the study group, indulging himself by imagining that her hug with Jeff was longer than those she shared with the others, that she looked a little reluctant to let him go ... but she did let him go, and then she was gone.

That had been the good part of the evening. Slater had decided all of a sudden that she wanted Jeff back, which had prompted Britta to decide that she too wanted to be with Jeff, and their jealous sniping had gotten so out of control that they both had ended up declaring their love for him in the middle of the Tranny Dance. The look on Jeff's face had been heartbreaking. Jeff was a man who had always prided himself on being able to talk his way out of any situation, but now he was lost, with no idea of what to say and no time to figure it out. The dean couldn't blame him for sneaking out when the melee started.

It was a nightmare. Any fondness Jeff might have developed for Greendale over the course of the year had surely been erased by the fiasco at the Tranny Dance, and without Annie on hand to get him to do things he was reluctant to do, he would never develop into the kind of campus leader the dean needed him to be. It was all so depressing. So much for next year being the start of a new golden age.

He glanced over at his computer monitor; the program he used to monitor the video feeds from the surveillance cameras was running, and by chance it happened to be showing the live feed from the camera aimed at Jeff's parking space, which sat empty save for a pile of broken glass. Seeing the empty space made him wonder when exactly Jeff had left, so he brought up the recorded video from that camera and started playback from 8:30 PM, which was about when he had seen Jeff make his escape from the Tranny Dance.

He sped through about 15 minutes of video before finding Jeff entering the frame ... carrying a pink duffle bag? Where ... wait, was that Annie? What was she doing there? He started tracing Jeff's path back across campus. The angle wasn't the greatest on some of the cameras, but that was definitely Annie walking alongside Jeff. It didn't make sense. He had watched her and Vaughn leave. He continued working backwards toward the cafeteria until he found the camera that had recorded Jeff and Annie approaching each other from opposite directions and stopping to talk.

This was an unexpected development. Did this mean Vaughn would be back too? If so, where was he? Perhaps ... oh.

Oh _my_.

Dean Pelton leaned back in his chair with a satisfied smile on his face. Maybe next year wouldn't be so bad after all.


End file.
